Neil Patel

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In a recent episode of the Dealmakers’ Podcast, Jake Schwartz, co-founder of General Assembly and Brave Health, shared his captivating entrepreneurial journey. From his formative years on a farm to spearheading successful startups, Jake’s story is a testament to resilience, adaptability, and a profound understanding of the business world.

In this blog post, we’ll delve deeper into key takeaways from Jake’s podcast interview and bring you even more valuable insights for aspiring entrepreneurs.

Listen to the full podcast episode and review the transcript here.

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Growing Up Near Portland

Jake’s parents moved from the East Coast to settle on a farm just outside of Portland. Although his father was an ER doctor,

Jake remembers their concept of being self-sufficient as having a year’s supply of gasoline, sheep, and chickens. He reminisces that his early years were not really as “cool” as he thought them to be.

Being a theatre kid, going to Yale for his education was an obvious choice. Jake’s focus was not just on going to the Pacific Northwest but more on realizing his full potential. Fresh out of college, he wanted to be a singer-songwriter and record producer.

Jake talks about his dream of having an office and a music studio equipped with a collection of instruments where he could write tons of music.

During the COVID, he had the time to do just that. In his opinion, entrepreneurship is much like songwriting, an interesting art form because it’s both incredibly creative but also very structured and disciplined.

Much like in songwriting, where moments of inspiration are shaped by meticulous craftsmanship, successful entrepreneurship requires a balance of innovative thinking and methodical execution.

Stepping into the World of Entrepreneurship

Jake’s experiences taught him that some industries are much more conducive to having a fruitful career and happiness and offer the potential to grow and develop, and some are not.

He recalls starting a series of small entrepreneurial ventures in the nonprofit performing art space.

They had a little music stage, a record label, and a roving art gallery. Pre-2008, Jake realized that a lot of people were working for private equity or hedge funds but were quickly crushed when the financial crisis hit.

Jake was determined to start his own venture instead of working for someone else. This attitude led him to take up several consulting gigs until he started General Assembly.

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Ideating General Assembly

Jake met Matt Brimer, a 22-year-old student who hosted a Yale entrepreneur meetup. Jake was impressed by the Yale business cards Matt was handing out. Soon, he teamed up with Matt along with one of his co-founders, Brad, Adam, and Mimi Chun.

The team started out in a classroom where they began running classes. That’s when they realized that they could do a better job than any business school, law school, or college at helping people find the jobs they were good at and wanted to do.

Jake and his co-founders were soon offering courses in coding for UX design, marketing, different types of software development, data science, and more. They had online and offline classes worldwide on over 30 different campuses on four different continents.

At this point, Jake and his team realized that they would need to raise more money and learn the art of storytelling. Soon enough, they raised $100M.

Along the fundraising journey, they also learned how venture capital, preferred shares, and equity capital work to the point where you get people to write checks and give you money in exchange for shares.

Navigating the Challenges of the American Education System

Jake talks about how he identified the key challenge of the American educational system as that of students needing to take on massive amounts of debt. He was determined that he wanted to come up with solutions that were different.

Jake found that they were attempting to fill the gaps in the skill sets that people had. The industry needed people with those skills to fill those slots, and not having the skills was preventing them from growing or expanding.

So, the next logical solution was to approach employers to fund their education. That’s how they could create a much more vertically integrated talent pipeline.

Jake came up with the vision of employers placing orders for talent upfront and for his company to use those orders to finance the education of their employees.

Since there was job assurance at the end of the courses, theirs was more of a vocational training system, which was very logical. That’s how they could streamline the staffing and recruitment industry, especially after acquisitions.

The concepts Jake and his co-founders came up with were so successful that they all made money–the employees whom Jake credits with doing the heavy lifting, founders, and top executives. Their company soon reached a valuation of $8M.

Lessons from General Assembly: The Art of Adaptation

Reflecting on the journey of General Assembly, Jake highlights the critical importance of adaptability. Successful entrepreneurs must be prepared to pivot when faced with challenges or changing market dynamics.

This ability to evolve and respond to new information is often the differentiator between thriving and stagnating in the competitive business landscape.

Entrepreneurial Grit: Lessons from Brave Health

The concept for Jake’s next venture started with a conversation with his dad and brother, both of whom worked in the healthcare sector.

They owned a few clinics focused on the Medicaid population and medically assisted treatment for opioid abuse. At this point, they realized that Medicaid was a key player and much more diverse.

With Brave Health, Jake and his team are revolutionizing access to mental health services for Medicaid recipients. This venture exemplifies the power of entrepreneurial grit and determination.

Jake has successfully made Medicaid-assisted care available to patients with chronic PTSD and other issues.

By leveraging technology and modern operational strategies, Brave Health is demonstrating that even in traditionally challenging sectors like healthcare, innovation and transformation are not only possible but essential, so much so that Jake has successfully raised $60M for the venture.

Storytelling is everything, which is something that Jake Schwartz was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend Peter Thiel (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.


Jake Schwartz’s entrepreneurial journey serves as an inspiration for aspiring business leaders. His insights into unit economics, redefining success, and the combination of creativity and structure provide invaluable guidance for navigating the complexities of entrepreneurship.

By embracing these lessons, budding entrepreneurs can embark on their own journeys with a clearer understanding of the path ahead. As you navigate the startup landscape, you can think back on Jake’s wisdom. Learn from his approach to each challenge with determination, creativity, and strategic thinking.

Listen in to the full podcast episode to find out more, including:

  • Mastering unit economics is essential for sustainable business growth.
  • True success transcends external validation and lies in making a meaningful impact.
  • Balancing passion with industry viability is crucial for entrepreneurial success.
  • Entrepreneurship demands a fusion of creativity and structured execution.
  • Adaptability is key – be ready to pivot in response to market dynamics.
  • Mentorship plays a pivotal role in guiding the next generation of entrepreneurs.
  • Entrepreneurial grit and innovation can revolutionize even the most challenging sectors, like healthcare.


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Neil Patel

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